It’s probably the wrong time of year to be addressing this issue, but in recent weeks I’ve seen a lot of five and six year-olds getting ready to start Kindergarten. Most were very excited and I was excited for them too. Also anxious. I hope they have a great experience, a wonderful, memorable year, but, like their parents, there’s always the worry that a bad first experience at ‘real school’ will color forever their attitude about school.

We all want what’s best for our children and sometimes it’s hard to know what to do. Do we let them date at 15? How old to get that cell phone? Do we let him (or her) play killer football? It can be tough.

One of the most far reaching and irrevocable decisions concerns at what age to start school. I’m lucky in that my birthday is September (as is one of my children’s), but for parents whose children are born in the summer or late spring, it is sometimes difficult to decide when to start Kindergarten. There is no simple answer.

There are several factors to consider and options to weigh. First, one should consider what school or school system your child will attend. In some private schools, a child with a late birthday (past May first) almost never starts first grade just after their sixth birthday. If your child plans to attend one of these schools, and they start first grade at a young age six, they will be younger than all their grade-mates, sometimes much younger, for twelve long years. No matter how smart they are, they may be emotionally and physically out-ranked for a long time.

In other private schools and most public systems, children are ‘held back’ only rarely. Your summer birthday child, in such a school will probably do just fine starting first grade at six and will find class mates of similar physical and emotional maturity.

But what if he already reads and needs the stimulation a preschool just doesn’t provide? This is an important consideration. Boredom is pretty sad and we all want our children to advance academically at the best pace for them. If they are academically ready to handle the demands of the classroom, many would ask, why wait?

Aside from academic readiness you also have to consider the child’s emotional maturity. This might be the most important and one of the more difficult factors to assess. Question your child’s preschool teachers, perhaps arrange for special testing (a part of the entrance process for some private schools) and take every opportunity to observe your child in settings with children of similar and older ages. Their emotional maturity may be more important than their academic ability.

Two other options come to mind. You may be able to put off the decision for a year or two. Consider placing your just-five child in a kindergarten different from the school that you eventually plan to use, private, parochial or public, ideally one that is smaller and quieter. If you decide at the end of that year that your child would benefit from another year in kindergarten, he or she can then attend kindergarten at a bigger/more challenging school, perhaps the neighborhood public elementary, without any sense of failure. There will be new classmates, a bigger cafeteria, etc. and you can avoid the idea that they have ‘failed’ kindergarten.

Or choose a flexible-grade school such as many Montessori schools employ. Your child might be placed in a class with K, first and second graders and be allowed and encouraged to advance academically as appropriate for them. When the time comes to transfer to a school with traditional grades, there will be options based on your child’s age, academic abilities and maturity level. It may be a lot easier to decide at an older age.

Of course the most important thing to do is give your child the assurance that you love them no matter what, that grades and school achievement don’t affect your support and affection for them and never will. Advocate for your child in whatever school you choose. You are their first and most important teacher.